Highly efficient organocatalytic kinetic resolution of activated nitroallylic acetates with aldehydes via conjugate addition-elimination. 2011

Raju Jannapu Reddy, and Kwunmin Chen
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 116, ROC.

A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a-i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition-elimination. The densely functionalized products 3a-o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a-i were recovered with good to excellent optical purity (up to 98% ee).

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